Sodium Hydroxide → Methyl 3-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylate

HRID 1773837ノート

反応式

HRID 1773837 の反応式
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:13](=O)[CH:14]=[C:15]([C:20]2[CH:25]=[C:24]([Cl:26])[C:23]([F:27])=[C:22]([Cl:28])[CH:21]=2)[C:16]([F:19])([F:18])[F:17])=[C:8]2[CH2:12][CH2:11][CH2:10][C:9]=12)=[O:4].[OH-:30].[Na+].[NH2:32]O.Cl>O.C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:13]2[CH2:14][C:15]([C:20]3[CH:25]=[C:24]([Cl:26])[C:23]([F:27])=[C:22]([Cl:28])[CH:21]=3)([C:16]([F:19])([F:18])[F:17])[O:30][N:32]=2)=[C:8]2[CH2:12][CH2:11][CH2:10][C:9]=12)=[O:4]

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 866937493-[3-(3,5-Dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid methyl ester

生成物 1

HCID 71472643Methyl 3-(5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylate収率 50,384.102%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Stir a mixture of 3-[3-(3,5-Dichloro-4-fluoro-phenyl)-4,4,4-trifluoro-but-2-enoyl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid methyl ester (25 g, 53.6 mmol), NaOH (8.6 g, 0.214 mol) and NH2OH—HCl (7.4 g, 0.107 mmol) in water (100 mL) and THF (200 mL) at room temperature for overnight. After removal of the solvent under vacuum, the solution is diluted with water and extracted with EtOAc (200 mL×3). The combined organic layer is washed with brine, dried over anhydrous Na2SO4 and concentrated by vacuum to afford 3-[5-(3,5-Dichloro-4-fluoro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-5,6-dihydro-4H-cyclopenta[c]thiophene-1-carboxylic acid methyl ester as a white solid (26 g), which is used directly in the next step without purification. MS (m/z): 483 (M+1).

後処理

  1. customAfter removal of the solvent under vacuum
  2. additionthe solution is diluted with water
  3. extractionextracted with EtOAc (200 mL×3)
  4. washThe combined organic layer is washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated by vacuum

出典と根拠

ORDレコード
ord-afa90f93cb5b4911994e5f6ccc26c9df
出典データセット
uspto-grants-2016_02
特許番号
US09255111B2

反応ノート

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